Should Should Not
by IndePUNdentThinking
Summary: Emma Swan has tried to keep her feelings for her best friend hidden for far too long, but should she take a chance on him? A Halloween-themed one-shot.


It was a bad idea.

Of course Emma knew it was a bad idea. Lusting after of the few friends she did have could never be considered a good idea.

She didn't know when exactly she started to have feelings for him. She was watching him play with Henry one day, his blue eyes sparkling with mischief as he told her son an outrageous story. Henry laughed along with the man, clapping his hands in glee. She felt herself smiling at the scene and then bam! She realized she was in love.

As soon as she realized what the warm feeling in her chest was, she tried to squash it. Love had only caused her sorrow. Sure, it gave her Henry, her adorable three-year old son, but it had left her brokenhearted and weary of letting anyone else in. It had even caused her to flee to a small town on the coast of Maine.

Enter Killian Jones, a charming and roguish man (his words, not hers) who swaggered (very literally) into her life. The boat tour operator had slowly become a shoulder to cry on (or punch, depending on how much she had to drink) and a surprisingly reliable babysitter now that Mary Margaret's nights belonged to David Nolan.

Initially the small brunette was apprehensive with Killian looking after Henry, but Emma was too tired to think of an alternative. Mary Margaret had suggested that she and David could stay in with Henry, but Emma refused to force Mary Margaret to look after a small child as a date. Especially because David, her fellow deputy, had been really looking forward to that date. Luckily for everyone involved, both the date and the babysitting went well, resulting in a permanent babysitting gig for Killian.

And now, several months later, she gets to watch her son try to teach Killian Jones, Ladies Man Extraordinaire, the words to the theme song from Paw Patrol!. Honestly, who wouldn't swoon? Henry was too adorable for words and Killian was handsome (a fact she begrudgingly came to accept). Still, she refused to give into her feelings, hoping that the loud thumping of her traitorous heart could only be heard by her.

"We're here! Sorry we're late!"

Mary Margaret barreled through the doorway into Emma's living room, her cheeks flushed. Emma couldn't help but smirk at her costume.

"Snow White? Really?"

Mary Margaret frowned.

"She's my favorite Disney Princess." She retorted defensively.

Emma continued to grin.

"Does that mean that Dav-"

Right on cue, David stumbled through the door, tripping over the edge of his sword, and Emma had to stifle a laugh. Killian did not hold back.

"Dave! What a regular Prince Charming!"

David straightened up, pushing his heavy cloak over his shoulders and scowling at Killian.

"Maggie!"

Henry toddled over to her, arms outstretched.

Mary Margaret cooed with delight.

"Oh he's so cute!" she gushed, picking him up and cuddling him.

Emma's smile softened, and she reached over to ruffle her son's hair, that was slightly tamed by the pair of floppy dog ears that he sported.

"Thanks for doing this," Emma started, but David waved her off.

"You deserve a night off." He said, wagging a finger at her.

"Indeed she does."

Emma nearly jumped at Killian's nearness. When did he sneak up on her? She turned to look at him, and found him staring at her intensely. She felt the heat rise in her belly and settle in her cheeks. Then he smirked and the moment was gone.

"Come Swan. Let your night of fun begin!"

* * *

It was a bad idea and she knew it.

Spending Halloween with the man you had a crush on? Who looked damn good in his ridiculous pirate garb (hook hand and all)? Emma clutched her coat and started to have regrets about her decision to go out. (and her decision to dress up as a doctor. Sure, it was easy to throw a white coat on top of her sweater and jeans and sling a plastic stethoscope around her neck, but she missed her red leather jacket)

The bar that Killian had picked was crowded with Halloween revellers, loud and scantily clad. Even the men wore minimal clothing, Emma noted, as she hung back near the bar waiting for Killian to arrive with their drinks. Just as her thoughts drifted back to him, he emerged from the crowd with his shirt mostly unbuttoned. Emma raised an eyebrow and he shrugged sheepishly.

"A lass got a hold of me…"

That was all Emma had to hear. She took her glass from him and downed the drink in one single gulp.

Killian looked at her with concern.

"Easy there, Swan."

She glared at him, and then reached for his drink.

When they tumbled out of the bar two hours later, Emma felt happier than she had in a while, a nice buzz settling in. Even the cold breeze of October couldn't dampen her spirits. Suddenly she felt Killian's hand around her waist and his mouth dropped to her ear, his hot breath tickling her neck.

"Alright there, Swan?"

His voice was low and husky, and it did terrible things to her, it really did.

"Never better!" she chirped, her voice sounding artificially bright even to her.

Seemingly satisfied by her answer, he moved away, but his arm remained around her waist.

Together they walked through the streets, laughing about a number of stupid little jokes that Emma knew she wouldn't remember tomorrow.

Finally they were outside her apartment, and Emma felt a pang of regret. Was the night over so soon?

Killian released her waist, his hand moving to grasp hers.

"Well, this is where I leave you, m'lady."

She let out an unladylike snort in response.

"Jeez, Jones. You're a pirate, not an 18th century gentleman."

He grinned at her and winked.

"I'm always a gentleman, Swan?"

She squared her shoulders and stepped toe-to-toe with him.

"Oh yeah? I seem to remember an incident with Rose…" she said teasingly.

She expected him to smirk and make a lewd comment about it, but instead he ducked his head and scratched the back of his ear.

"Ah well, that was a long time ago, Swan. I'm a changed man."

"Oh really?"

"Yes, really."

"So no more one night stands?"

"Nope."

"No more outrageous flirting?"

"Only with one person."

"And who would that be?"

"Guess."

She hadn't realized how close she was to him until he responded, his nose almost touching hers. She didn't move away though. Her hands rose to grasp the lapels of his jacket, and his eyes followed the movement, before moving up to stare at her lips. He moved closer, his nose now grazing hers.

"We shouldn't," Emma whispered as his mouth drew closer.

"We shouldn't?" he asked, pressing a kiss to the corner of her lips.

Emma pressed herself closer into him, and his arms encircled her and pulled her even closer.

"Or maybe we should."

Before Killian could respond, her lips crashed into his, pressing a fierce kiss upon them. Killian was momentarily stunned, but responded enthusiastically.

Emma's heart soared. It was even better than she had imagined. Her body felt like it was on fire, like it was burning up to keep her warm. Her hands rose up to tangle themselves in his hair, and she sighed against his lips. She felt him smile in response, and they broke apart to take a deep breath.

Killian chuckled as he dropped a kiss to her forehead.

"God knows how long I've been waiting to kiss you, Emma." He said, as he dropped his head to press a hot kiss to her neck.

Emma, distracted by the trail of kisses he was leaving on her jaw, almost missed his confession.

"You have?" she asked incredulously. When he didn't respond, she tugged sharply in his hair, causing him to groan and pull his head back. She poked him in the chest.

"Explain, buddy."

He smiled, tucking a loose strand of hair behind her ear.

"Swan, I've been in love with you for a year."

He announced this so casually that Emma momentarily thought that she misheard him.

"In love…a whole year?" she asked.

He laughed.

"Yes Swan. You were too dense to notice."

She swatted his shoulder, and he laughed harder.

"Seriously though. I wanted to say something…but I didn't know how you felt. And with the lad and everything else…"

He was starting to ramble, Emma realized, and she cut him off with another kiss.

"You're ridiculous, you know that?" she informed him, as they caught their breaths for a second time. "I can't believe I love you."

As soon as the words left her lips, his mouth descended on hers, and he lifted her into the air. Emma's shrieks of laughter filled the night air.

* * *

Half an hour later they made their way inside, with disheveled hair and identical grins. David looked up from his position on the couch and took in their appearances. He smirked at them, causing the grins to turn to blushes.

"Looks like you both got a treat tonight."


End file.
